Ethanol → HCID 11719313, compound

HRID 1992987Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:4]([O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23]CC)=[O:22])=[C:15]([C:26]([F:29])([F:28])[F:27])[CH:14]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CCO.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[C:3]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:4]([O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[C:15]([C:26]([F:29])([F:28])[F:27])[CH:14]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 70 °C

Procedure

The saponification procedure described in Example 1 (Step 10) was followed. Ethyl (2E)-3-[4-[(3-methyl-2-phenyl-1-naphthalenyl)oxy]-2-(trifluoromethyl)phenyl]-2-propenoate (241) (0.070 g, 0.147 mmol) was dissolved in 1:1 THF:EtOH (6 mL). To the above mixture was added 1 N NaOH (1 mL, excess) at room temperature followed by heating at 70° C., with stirring, for 30 min. The reaction mixture was cooled at RT, subjected to standard work up and purification to afford 0.065 g (99%) of the title compound (242) as a white foam. IR (film) 3058, 1693, 1606, 1491, 1313, 1165, 1128 cm−1. 19F NMR (282.2 MHz, CD3OD): δ −60.98. 1H NMR (400 MHz, CD3OD): δ 7.91 (br d, J=8.0 Hz, 1H), 7.84 (d, J=16.0 Hz, 1H), 7.79 (s, 1H), 7.77 (d, J=8.8 Hz, 1H), 7.64 (d, J=7.6 Hz, 1H), 7.52 (dd, J1=7.2 Hz, J2=7.2 Hz, 1H), 7.43 (dd, J1=7.6 Hz, J2=7.6 Hz, 1H), 7.28 (m, 3H), 7.15 (br s, 1H), 7.14 (s, 1H), 6.90 (s, 1H), 6.76 (d, J=8.4 Hz, 1H), 6.33 (d, J=16.0 Hz, 1H), 2.26 (s, 3H).

Workup

temperatureThe reaction mixture was cooled at RT
custompurification

Sources & evidence

ORD record: ord-b3793882c95545839948e5dd0cb7c77a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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